VirnetX Holding Corporation is a patent holding firm that has a pretty impressive portfolio of IP (Intellectual Property) related to wireless networking and LTE technology. And as you’d expect, it’s not afraid to use it.

The company is currently entangled in legal battles with the likes of Cisco and Siemens, and it actually took more than $100 million from Microsoft in court. And according to a new report, it just took Apple for 3x that…

“A federal jury in Texas on Tuesday ordered Apple to pay patent holding firm VirnetX $368 million in a patent lawsuit. Apple declined to comment, but is expected to appeal. A VirnetX representative was not immediately available for comment.

VirnetX also has filed complaints with the U.S. International Trade Commission against Apple, alleging that its iPhone, iPad and Mac products violate the company’s patents.”

So not only will Apple have to pay close to $400 million to VirnetX in damages, but it also now has to worry about the ITC banning several of its products that were accused of patent infringement from sale in the US. Ouch.

VirnetX’s suit against Apple was first filed in November of last year. The company claimed Apple’s iPhone 4S infringed on its “Method for Establishing Secure Communication Link Between Computers of Virtual Private Network” patent.

Of course, like Apple’s big legal victory against Samsung in August, this case is far from over. Apple will obviously appeal the ruling. And even if it doesn’t win, it should be able to trim quite a bit off of the $368 million fine.

I would say, “what goes around comes around.” But VirnetX is a company whose sole purpose is to buy patents and leverage them against other companies for money. At least Apple makes some cool stuff on the side.